Organic photoredox-catalyzed unimolecular PCET of benzylic alcohols

Proton-coupled electron transfer (PCET) is a crucial chemical process involving the simultaneous or sequential transfer of protons and electrons, playing a vital role in biological processes and energy conversion technologies. This study investigates the use of an organic photoredox catalyst to facilitate a unimolecular PCET process for the generation of alkyl radicals from benzylic alcohols, with a particular focus on alcohols containing electron-rich arene units. By employing a benzophenone derivative as the catalyst, the reaction proceeds efficiently under photoirradiation, achieving significant yields without the need for a Brønsted base. The findings highlight the potential of this unimolecular PCET mechanism to streamline radical generation in organic synthesis, offering a more efficient and flexible alternative to conventional methods.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d4sc07048h
Citations
15
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
14.04

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article

Organic photoredox-catalyzed unimolecular PCET of benzylic alcohols

Hirohisa Ohmiya, Tomotoki Matsuo, Yuto Sumida, Masaki Sano
15 citations
Chemical Science
Radical Photochemical Reactions
14.04
article

Organic photoredox-catalyzed unimolecular PCET of benzylic alcohols

Hirohisa Ohmiya, Tomotoki Matsuo, Yuto Sumida, Masaki Sano
article en
15 citations

Abstract

Proton-coupled electron transfer (PCET) is a crucial chemical process involving the simultaneous or sequential transfer of protons and electrons, playing a vital role in biological processes and energy conversion technologies. This study investigates the use of an organic photoredox catalyst to facilitate a unimolecular PCET process for the generation of alkyl radicals from benzylic alcohols, with a particular focus on alcohols containing electron-rich arene units. By employing a benzophenone derivative as the catalyst, the reaction proceeds efficiently under photoirradiation, achieving significant yields without the need for a Brønsted base. The findings highlight the potential of this unimolecular PCET mechanism to streamline radical generation in organic synthesis, offering a more efficient and flexible alternative to conventional methods.

Chemical ScienceVol. 16(7)
Kanazawa University (JP), Kyoto University (JP), Kyoto Bunkyo University (JP), Kyoto University Institute for Chemical Research, The University of Tokyo (JP)
Japan Society for the Promotion of Science, Japan Science and Technology Agency, Institute for Chemical Research, Kyoto University
Affordable and clean energy
Openalex Percentile: Top 1%
Radical Photochemical Reactions
14.04
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